Hypervalent Sulfur Derivatives as Sulfenylating Reagents: Visible-Light-Mediated Direct Thiolation of Activated C(sp2)-H Bonds with Dihalosulfuranes

被引：0

作者：

Kuznetsova, Elizaveta A. ^{[1
,2
]}

Rysaeva, Regina R. ^{[3
]}

Smolobochkin, Andrey V. ^{[1
]}

Gazizov, Almir S. ^{[1
]}

Gerasimova, Tatyana P. ^{[1
]}

Gerasimova, Daria P. ^{[1
]}

Lodochnikova, Olga A. ^{[1
]}

Morozov, Vladimir I. ^{[1
]}

Vatsadze, Sergey Z. ^{[4
]}

Burilov, Alexander R. ^{[1
]}

Pudovik, Michail A. ^{[1
]}

机构：

[1] Russian Acad Sci, FRC Kazan Sci Ctr, Arbuzov Inst Organ & Phys Chem, Kazan 420088, Russia

[2] Kazan Natl Res Technol Univ, Kazan 420015, Russia

[3] Kazan Fed Univ, Butlerov Chem Inst, Organ Chem Dept, Kazan 420008, Russia

[4] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 20期

基金：

俄罗斯科学基金会;

关键词：

YLIDE TRANSFER; HYDROLYSIS; SULFOXIDES; RADICALS; SALTS;

D O I：

10.1021/acs.orglett.4c01305

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In contrast to hypervalent iodine compounds, the chemistry of their sulfur analogues has been considerably less explored. Herein, we report the direct C-H bond thiolation of electron-rich heterocycles, arenes, and 1,3-dicarbonyls by dichlorosulfuranes under mild conditions. Mechanistic studies and density functional theory calculations suggest the radical chain mechanism of the disclosed transformation. The key to success is attributed to a strikingly low S-Cl bond dissociation energy, which enables the generation of radical species upon exposure to daylight.

引用

页码：4323 / 4328

页数：6

共 24 条

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